The purpose of this paper is to bring together two thinkers that are concerned with the limits of what can be said, Wittgenstein and Maimonides, and to explore the sense of the good life and of the mystical to which their therapeutic linguistic work gives rise. I argue that despite the similarities, two different senses of the "mystical" are brought to light and two different "forms of life" are explicated and recommended. The paper has three parts. In the first part, I discuss certain key components in Wittgenstein’s early philosophy and the sense of the mystical to which they give rise. In the second part, I discuss Maimonides’ negative theology and its implications for his conception of the ’via mystica’. I end, with a discussion of the relation between the two ideals and its significance